Source: CNBC

I was watching a clip the other day of Gary Vee, when something he said really resonated with me. He said we really build our own jails in our mind that keep us trapped in the expectations that we set for ourselves. His point was that it’s ok to change your mind. He was referring to a strategy of giving away money to the first people to comment with a particular hashtag on his posts but he felt it was just divulging into greed that distracted from his message. So he scrapped the project.

A few of us get really lucky in life. We work hard but we also encounter the right circumstances at the right time which helps us to achieve some great things. It could be making the right social connection to which presents a great opportunity or it could landing in the right industry at the right time.

The Opportunities Right in Front of Us

Case in point my college roommate. He didn’t really know what he wanted to do but he had studied cell biology because he liked it. After college a drifted around odd jobs but on the side was doing something he really loved: improv acting. After a few years of post college odd jobs and working on his passion on the side, he decided to take the leap and move to Chicago to work at the Mecca of improv: Second City in Chicago.

You may think that you know where this is headed next. He followed his dream and took a chance, which landed him in Second City, which produced another opportunity via someone he met there which catapulted him to super stardom. You may expect me to say my old roommate is Steve Carroll or Jordan Peele but you would be mistaken. You may think this story is about him getting into acting at the right moment which changed the trajectory of his life. In fact, the move did end up changing the trajectory of his life and his career and he did end up moving to Hollywood but in a completely different manner than you would have expected.

That’s because as he was working at Second City, he still needed to pay his bills so he applied for a boring old day job at a small local company. This small local company ended up being what is today Groupon. At the time it only had a few employees but it paid the bills and allowed him the flexibility to do his improv work on the side.

Slowly but surely the firm grew while his improv career, although somewhat successful, plateaued. Things changed when Groupon went public. He didn’t get rich instantly, as some have done in the tech boom, but he did gain notoriety within the tech industry for the important role he had played in helping Groupon grow from a fledgling company to a publicly owned one in the matter of a few short years.

Soon he was being courted by tech companies all over the US. He worked for a time for a few companies in the Midwest, including Uber before they went public (in fact, due to his experience there, I knew they were going to have ethics issues long before they became public) until Snapchat lured him out to LA. After a stint there he was again courted to work at Netflix and is currently living in Hollywood. He still works on the more technical side of things but ironically is now working a well paying job at a film company in Hollywood, years after making the leap to Second City.

In the end the decision that changed his life was not necessarily acting, it was to take the leap and go all in on something, even if through that path, the end result wasn’t exactly what he was looking for. This brings me back to my original point about building jails within our minds for ourselves. Too often, many of us set boundaries within our current circumstances that dictate where our lives are allowed to go when in reality the only person that is making these boundaries is us.

Flash Forward to Today

In my own situation, getting laid off and getting divorced have been some of the best and most important experiences in my life and they happened all within a relatively short timeframe of each other. These events forced me to step back and confront my fears: fears of what others would think, fears of not having enough money and fears of where my life was headed and the uncertainty that would come with it. I learned to not fear any of that. I learned that stories like my college roommates are very possible if you are willing to break out of your jail and take the leap.

When we are younger, I think we tend to be more aware of the possibilities and potential opportunities in life. We have so much time left which means more than enough time to make mistakes. We also can afford to be selfish. Move to a new city without consulting anyone. Move to a new job just for a different atmosphere or different experience or choose to take time for ourselves to travel or work on a project.

As we get older though, we tend to have more responsibilities: children, a spouse aging parents etc. This contrasts with the freedom we may have had when we were out of school, younger or single. We also hopefully tend to move up in our careers a bit and make more money. In my case I quickly made much more money in my career at an early point, more than I had though possible just a few years before.

At this time many people tend to take a breather, rest on their laurels. The hard work is over they may say to themselves, I’ve made it and I deserve to take things a little slower. I know because I have been there too. The ambition and the energy to move up at work is diminished. You may have reached a goal in your business and the desire to keep pushing recedes. At this point hopefully you like the path you have chosen and can derive a lot of happiness from your day to day work, but this isn’t the case for many of us. Many of us were never completely thrilled with what we had to do for work and we are comfortable now so we set in to what is sometimes called the mid-career malaise.

This is probably more difficult to break out of than any other phases of your life. For the first time you may have something to lose and you may have a number of people depending on you. Change could upset them and bring you into conflict with them. You would like to keep your home life stable and provide for people, upsetting that may involve more risk than you are willing to take.

On the flip side, this may also impact your performance at work or at your job. Expanding your business or moving up involves taking risks, playing offense. If you aren’t playing offense you are on defense and those around you will start to notice, whether you are aware of it or not. People start to play defense out of fear. I have come this far, I have to protect what I have managed to get so far.

I would argue however, that we lose more in the long run by playing defense than by going on offense. Taking a risk with your business could produce a huge setback or even sunk it. Likewise taking a risk as a senior person at a job could blow up in your face and get you let go.

In this sense it’s that old fear of failure which ironically comes back to haunt us mid-career and may be even stronger than the fear of failure many of us had when we were younger.

Breaking Out

Some of the biggest success stories of our time were made by people deciding to break out of the mid-career malaise. The most famous probably being Jeff Bezos, who quit a lucrative job at a hedge fund to start Amazon. Or take for example the founder of Zoom, Eric Yuan, who had a lucrative six figure job but didn’t find himself happy. Yuan recently became a billionaire as Zoom went public.

These are exceptional stories and ones where everything went right so I don’t want to paint the picture that this is what’s ins tote for you if you quit your well paying job. Indeed you may fail spectacularly. The point is more about taking the chance rather than the outcome. I wasn’t surprised to hear Jeff Bezos remark that the reason he decided to quit his job was not because he knew he would be a success but because he didn’t want to be in the retirement home looking back on his life and being filled with regrets of what he could have done.

This is probably the key vision and perspective most people have to break out of the mid career malaise. Taking the long view of your life to break out of the mental jail that many of us have put ourselves in. To find the courage to do something new, learn something new and continue to push the boundaries and challenge ourselves.

The changes in my own life jolted me into that long term perspective and pushed me to start writing again and considering what I wanted next for myself. This has involved signing up for the final level of the CFA exam which I failed many years ago. It’s not simply the challenge of the exam but the potential marketing use of the designation should I choose to break out on my own and manage people’s money through my own business.

Sticking with social media has helped too. I have started to play with video editing and am working on shorts that discuss the history of markets and economics, something which I like to do even if it doesn’t pay me.

Do I know where any of this will lead? Right now I have an idea but it may not turn out as planned and that’s ok. Knowing that I am using my current job as a stepping stone to something I want later keeps me engaged and keeps me motivated even though I know I won’t be there forever. It helps me deal with difficult co-workers and clients and helps me treat people more kindly because I have a long term vision for the contentment of my life in motion. This vision doesn’t involve any need to step on people for short term gain. It leaves me day to day more happy knowing that I am on a path to taking a risk which I won’t regret. Even if I console yelp fail and fall flat on my face, when I am in the nursing home I can look back on it and say hey, I didn’t make it big but I sure did everything in my power to try to. In the long run, that may be worth more than settling for what I have right now.

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